P
US5208243AExpiredUtilityPatentIndex 92

5-isoquinolinesulfonamides

Assignee: ADIRPriority: Jul 31, 1991Filed: Jul 30, 1992Granted: May 4, 1993
Est. expiryJul 31, 2011(expired)· nominal 20-yr term from priority
Inventors:PEGLION JEAN-LOUISVILAINE JEAN-PAULVILLENEUVE NICOLEJANIAK PHILIP
A61P 7/02A61P 9/06A61P 9/10A61P 9/12A61P 9/00A61P 9/08A61P 15/00C07D 401/12C07D 405/14A61P 13/02A61P 11/00A61P 1/00
92
PatentIndex Score
40
Cited by
2
References
9
Claims

Abstract

Compounds of formula (I): ##STR1## with R 1 , R 2 , U, X, Y, Z, n, m, p and r as defined in the description. Medicinal products.

Claims

exact text as granted — not AI-modified
We claim: 
     
       1. A compound selected from those of formula (I): ##STR18## in which: n is 0 or 1 to 4 inclusive, m and p are 1 to 4 inclusive, it being understood that the sum m+p is 2, 3, 4 or 5,   r is 1 to 6 inclusive,   R 1  represents hydrogen, chlorine, or hydroxy,   R 2  represents hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, lower cycloalkylalkyl, phenyl, or phenyl loweralkyl,   X, Y or Z, which are identical or different, represent hydrogen, halogen, or a group chosen from lower alkyl, lower alkoxy, nitro, amino, cyano, acetamido, carboxamido, or X and Y, or Y and Z, together form, with the 2 carbon atoms of the phenyl nucleus carrying them, a furan, dihydrofuran, or benzene ring,   U represents a single bond, oxygen, sulfur, or a group chosen from: carbonyl, sulfinyl, sulfonyl, --NH--CO--, --CO--NH--, or --O--(CH 2 ) r'  --O--, with r' meaning 2 or 3, --(CH 2 ) r"  --O--(CH 2 ) r"'  --  with r" and r"' meaning 1 or 2, and ##STR19##  where R 3  represents: - hydrogen,   - formyl,   - --A, --CO--A, or --CO--O--A, with A meaning lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, or cycloalkylloweralkyl,   - --(CH 2 ) q  -phenyl or substituted --(CH 2 ) q  -- phenyl, with q meaning 0 or 1 to 4 inclusive,   - --CO--phenyl or substituted --CO--phenyl,   - --CO--O--phenyl or substituted --CO--O--phenyl,   - --CO--NR 4  R 5   where     R 4  and R 5  : - which are identical or different, represent hydrogen or a group chosen from lower alkyl, lower alkenyl, lower alkynyl, phenyl or pheny, loweralkyl, - or form with the nitrogen atom carrying them a saturated ring with 4 to 7 members, 3 to 6 of which are carbon atoms,       it being understood that the term "substituted" which applies to the groups --(CH 2 ) q  --phenyl, --CO--phenyl, or --CO--O--phenyl means that these groups may be substituted by one or more radicals chosen from: lower alkyl, lower alkoxy, hydroxyl, a halogen atom, and trifluoromethyl,   it being understood that the terms "lower alkyl" and "lower alkoxy" mean linear or branched saturated carbon groups having 1 to 6 carbon atoms, inclusive, that the terms "lower alkenyl" and "lower alkynyl" denote linear or branched unsaturated groups having 2 to 6 carbon atoms, inclusive,   - that the term "cycloalkyl" denotes a saturated carbon ring having 3 to 8 members, inclusive,     the optical isomers thereof which may exist, as well as, where appropriate, its addition salts with a pharmaceutically-acceptable acid.   
     
     
       2. A compound of claim 1, in which m and p each represent 2, as well as, where appropriate, its addition salts with a pharmaceutically-acceptable acid. 
     
     
       3. A compound as claimed in claim 1, which is N-methyl-N-{1-[4-(p-fluorophenoxy)butyl]-4-piperidyl}-5-isoquinolinesulfonamide, as well as its addition salts with a pharmaceutically-acceptable acid. 
     
     
       4. A compound as claimed in claim 1, which is N-methyl-N-{[1-[3-(p-fluorophenoxy)propyl]-4-piperidyl]methyl}-5-isoquinolinesulfonamide, as well as its addition salts with a pharmaceutically-acceptable acid. 
     
     
       5. A compound as claimed in claim 1, which is N-methyl-N-{[1-[3-(p-fluorophenoxy)propyl]-3-pyrrolidinyl]methyl}-5-isoquinolinesulfonamide, its optical isomers, as well as its addition salts with a pharmaceutically-acceptable acid. 
     
     
       6. A compound as claimed in claim 1, which is N-{[1-[3-(p-fluorophenylamino)propyl]-4-piperidyl]methyl}-5-isoquinolinesulfonamide, as well as its addition salts with a pharmaceutically-acceptable acid. 
     
     
       7. A compound as claimed in claim 1, which is N-methyl-N-{[1-[4-(p-fluorophenyl)butyl]-4-piperidyl]methyl}-5-isoquinolinesulfonamide, as well as its addition salts with a pharmaceutically-acceptable acid. 
     
     
       8. A pharmaceutical composition useful for combating tissue pain containing, as active ingredient, an effective amount of at least one compound as claimed in claim 1, in combination with one or more pharmaceutically-acceptable excipients or vehicles. 
     
     
       9. A method for treating a living animal body afflicted with a condition due to or linked to tissue pain comprising the step of administering to the said body an amount of a compound of claim 1 which is effective for the alleviation of the said condition.

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